Jester Sailing Adventures

This review is long over due. I went on a trip in November 2011 to St. Thomas and this was the best part of the trip. We had the entire boat to ourselves and it was a breathtaking trip. The sailing part was great and the Captain was very friendly and even cooked us lunch. I would definitely recommend Jester for your next sailing adventure if you’re ever in the St. Thomas area. He made our trip better than expected and we got lucky having the entire boat to ourselves.

The greatest part of the trip. Captain Jim was better than ever could be expected. Celebrated a birthday on the boat and he brought a birthday cake on board as a surprise. Expensive, but worth every penny. It was a chance of a lifetime. Thanks Captain Jim

The first thing we knew we wanted to do when we planned our trip in St. Thomas was to take a day sailing trip. We scoured the internet, but didn’t have a ton of luck finding info. We finally read about Jester Sailing and emailed him. He was very helpful and explanatory and we decided to book it. His boat is a 38′ sailing boat and holds up to 6 people. We decided to book the entire boat for the 4 of us so that it wouldn’t ever feel crowded though.
We met him in on the beach of Secret Harbor at 10am and he took us out to the boat in his dingy. It was a gorgeous day and I knew it was going to be a fantastic time. He started us all out with a morning cocktail and my friends raved over his famous «Jester Juice» cocktail. (I’m not a fan of coconut so I had a rum punch and it was awesome too!) We headed over to Honeymoon Bay on St. John and spent some time on the beach, did some snorkeling and saw a sting ray. At lunchtime, he came and picked us up again on the dingy and brought us back to the boat. He had grilled some chicken and had a pasta salad and corn with it. It was awesome! He said for many years, he’d been in restaurnant management as well, so that explains why he’s such a great cook!
After Honeymoon Bay, we headed over to Christmas Cove and did more snorkeling– there were tons of fish! He dove down and found a conch on the ocean floor and pointed out lots of fish I would have totally missed! I hated having to come back in to shore, but it was truly the perfect day and Jim did such an excellent job.